Hydrochloric Acid → HCID 77230603, compound

HRID 1520046Notes

Reaction equation

HRID 1520046 reaction equation
[OH-].[Na+].[C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([O:16]C)=[O:15])[CH:12]=2)[N:7]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][O:19]2)[N:6]=1)#[CH:4].Cl>CN(C=O)C.CO>[C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([OH:16])=[O:15])[CH:12]=2)[N:7]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][O:19]2)[N:6]=1)#[CH:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 77230604HCID 77230604, compound

Product 1

HCID 77230603HCID 77230603, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium hydroxide (100 mL; 5.0 M; 500 mmol; 18.1 eq.) was added in one portion to a solution of methyl 3-ethynyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-5-carboxylate (7.9 g; 27.7 mmol; 1.0 eq.) in DMF (100 mL) and MeOH (100 mL). The reaction mixture was stirred at RT for 1 h, then poured into a 1N HCl solution (pH 1) and extracted with DCM. Combined organic phases were washed with brine, dried over magnesium sulfate, filtered and concentrated. The brown solid obtained was triturated with MeOH to give the title compound as a red solid (4.83 g, 65%). 1H NMR (300 MHz, DMSO-d6) δ 13.09 (s, 1H), 8.35-8.28 (m, 1H), 8.04 (dd, J=8.9, 1.5 Hz, 1H), 7.90 (dd, J=8.9, 0.6 Hz, 1H), 5.95 (dd, J=9.5, 2.3 Hz, 1H), 4.73 (s, 1H), 3.94-3.84 (m, 1H), 3.83-3.69 (m, 1H), 2.43-2.27 (m, 1H), 2.09-1.93 (m, 2H), 1.83-1.65 (m, 1H), 1.64-1.52 (m, 2H). HPLC (max plot) 99.5%; Rt %3.17 min. UPLC/MS: (MS−) 269.3.

Workup

  1. extractionextracted with DCM
  2. washCombined organic phases were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe brown solid obtained
  7. customwas triturated with MeOH

Sources & evidence

ORD record
ord-7be231346ec7430daa3c1f9666ea134c
Source dataset
uspto-grants-2015_07
Patent number
US09073892B2

Reaction notes

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